Water → m-Nitrophenethyl acetate

HRID 1247640Notes

Reaction equation

HRID 1247640 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[CH2:7][CH2:8][OH:9])([O-:3])=[O:2].[C:13](OC(=O)C)(=[O:15])[CH3:14].O>N1C=CC=CC=1.C(OCC)(=O)C>[N+:1]([C:4]1[CH:5]=[C:6]([CH2:7][CH2:8][O:9][C:13](=[O:15])[CH3:14])[CH:10]=[CH:11][CH:12]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 1040583-Nitrophenylethyl alcohol

Product 1

HCID 110451m-Nitrophenethyl acetate

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

3-Nitrophenethyl alcohol (55 g, 0.33 mol) (Aldrich) was dissolved in pyridine (1.2 L) (Aldrich). Acetic anhydride (215 mL, 2.14 mol) (Aldrich) was added slowly, and the mixture was stirred overnight at room temperature (TLC: 30% ethyl acetate in hexanes showed complete conversion). Ice and water (200 mL) were poured into the reaction mixture. The mixture was diluted with ethyl acetate, then successively washed with aqueous 1N hydrochloric acid (pH=˜1), water, and brine. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to give acetic acid 2-(3-nitro-phenyl)-ethyl ester as a yellow oil. (Yield 58.86 g, 0.28 mol, 85%).

Workup

  1. washsuccessively washed with aqueous 1N hydrochloric acid (pH=˜1), water, and brine
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-eab731bad28b4210878072b959039a78
Source dataset
uspto-grants-2006_10
Patent number
US07129351B2

Reaction notes

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